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From my experience, loot drops more frequently if you kill enemies around your level range (by weapon).
The level range is determined by the first pirate to engage combat with the enemy, and survives. If he/she gets knocked out, the enemy will go for another pirate, and he will be the level determinant.
Again, this is based on my very observational experience with fighting others with different level ranges, and my own personal experience with different weapon-leveled pirates.
My advice? Get a weak pirate to sweep those Veterans at the Marching ground, and finish them off yourself for massive lootage. Don't bother doing it yourself if you're too strong.
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